


Rags And Riches

by hellhoundsprey



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Bottom Dean, Class Differences, Domme Amara, Heterosexual Dean, I REGRET NOTHING, Multi, Sex Toy Dean, Sibling Incest, sub chuck
Language: English
Status: Completed
Published: 2016-06-04
Updated: 2016-06-04
Packaged: 2018-07-12 05:51:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,752
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7087807
Author URL: https://archiveofourown.org/users/hellhoundsprey/pseuds/hellhoundsprey
Summary: <blockquote class="userstuff">
              <p>Dean befriends Chuck to get closer to his hot sister. Things don't go as planned.<br/>(Everyone is in their late twenties.)</p>
            </blockquote>





	Rags And Riches

Chuck’s mouth tastes like beer and pretty much nothing else, just beer, and maybe it’s good that there’s not some kind of ‘guy’ taste in there; maybe that’s what allows Dean to keep going. For someone who can barely get an entire sentence out without stuttering at least once, Chuck actually isn’t such a bad kisser. Pretty good, actually. Damn.

She is close; Dean can feel the warmth of her body. She doesn’t touch though, at least not him. Her hand must still be on top of Chuck’s thigh. God. This is humiliating. Frustrating. Dean is buzzing, the itch in his fingers only heightened with the irritation of a beard that isn’t his own grazing his chin, his cheek, lips. He squeezes his eyes and fists his hands harder – into what again? The sofa? His own jeans? He’s lost direction at some point.

How did they get here anyway?

Maybe it’s better to roll the tape back. Maybe two months back – yeah, two months, right? Yeah, Dean remembers clearly. The first breathtaking sight, the first throb between his legs, under his fingernails. The first eye contact easily becomes a first flirt, the first step. It was different with her, though.

Oh, she’s a lady. And not the nasty kind of girl you only call ‘lady’ to make her giggle and punch your shoulder for being so greasy, to flatter her, croon her.

Oh, no. Amara is nothing like that.

She had looked him straight in the eye while she strode past, her long hair in perfect curls and bouncing with every step just like her neatly covered but clearly sizeable tits. She had class, immensely so, and the fact that she returned his glance (well, scratch that – his _stare_ ) made every ounce of Dean’s ego swell to twice its size.

And then she faced away. Walked away.

Dean was already standing, waiting for the bus to finally come. If not, he would have gotten up from his seat already, just from this tiny chance she offered with the eye contact, the tiny window she had opened between the two of them right then and there. As things were, his one leg was already half-bent for a step forward, his arm slightly extended, all the while she was already gone.

Dean felt – and clearly also looked – like a complete idiot.

Call him spoiled, sure, but Dean Winchester usually doesn’t have to fight for the first contact. Maybe for a number a little, yeah, and some girls demand to be dined and wined, sure; Dean’s a gentleman when he has to and if she’s a cute thing he’s glad to make the effort. But not even this? Not even a chance to ask for a name, to introduce himself, to make an offer? Nothing?

Call him melodramatic, sure, but that evening Dean Winchester paid two extra rounds for his buddies to make them receptive enough for his whining and general complaints. The crowd of them had gone from analyzing to comparing similar experiences to being offended to starting to call the girl mean names over the span three rounds. Just when the fourth arrived and Dean started with, “Y’know, if I ever see that _bitch_ again,” out of all people, it was Chuck who spoke up.

Chuck’s not really the brightest of them, or the loudest, or the funniest. He’s... well, he’s kind of with them only because someone pitied him and begged the others to have a heart and include him in their weekly pub tours. A pity-buddy. Doesn’t speak much and when he does he ruins his own jokes, chokes on something. It’s pathetic, really. Nerdy, weird; he’s a writer or something, Dean didn’t even really know since he never talked to the guy anyway.

But Chuck, this tiny little unimportant piece of shit, sat there like someone offended his dead mother or something, almost empty beer clutched in his hands, and he called out (actually loud enough for everyone to notice him, for once), “I-I’m pretty sure you’re talking about my sister.”

And just like that, Chuck ‘very likely to have his mother ironing his underwear’ Shurley turned into Dean’s bff. Dean made sure prior to such a commitment, of course, by asking for proof in the form of photos. They crowded the poor fool, almost bashed each other’s heads in to catch a glimpse, and, yeah, fuck, the girl _was_ Chuck’s sister. Better yet (or worse?) – fraternal twin. However that shit worked, but thank god Amara (her name, which Chuck supplied without much thought to what Dean could do with that information) looked nothing like her brother. Actually, the two of them seemed like from two completely different solar systems. How could two siblings turn out so unalike? Dean’s little brother and him were a story of their own as well, yeah, but this was a completely new league right there.

Chuck had to look up his own phone number in his address book when Dean asked him for it and got it wrong twice. Dean decided not to mind, to be very blind for the time coming, to be strong and get through this because it would be so _very_ worth it.

The fantasies concerning Amara (and what an exotic name for a mysterious beauty like her, too!) became wilder and more complex night by passing night. Dean tried every possible way she could turn out to be like – slutty, virgin-shy, brutal, funny, awkward – and _everything_ seemed possible. And he would soon be able to get the real thing.

It was and is unclear to Dean if Chuck knows or knew they only hang out because he wants to bang his sister. In order not to be too rude, Dean spent several drinks or movies or whatever he hoped would turn Chuck contended (which they all did; the guy really wasn’t picky) before he started digging for the gold. A sly smirk and a, “Think you could introduce me to her?” was the first attempt he started.

Chuck was at his fifth beer at that time. He could take least of everyone of their group even though he clearly improved since he started hanging out with them. He let out a nervous laughter, quickly looked away, and that was not good. Not at all. “Uhm, who?”

Dean kept his face over the first hints of annoyance. “You know who.”

“A-Amara?” More laughter, hands through hair first and beard later. Watching it was bad enough to make Dean uncomfortable, too. “I, uh, I dunno if that’s such a... good idea, Dean...”

“Why not?” More affront. Elbow out, closer to Chuck over the slightly crooked bar table. Eye contact on full force. “Am I not good enough or somethin’? Not her type?”

What Chuck gave him was the closest meeting between painful and pitiful, and it was directed at Dean.

Chuck. Pitied. Dean.

The entire idea seemed pointless all of a sudden. Dean came down, hard, and realized he had just spent twenty bucks this evening alone on the company of a guy who deeply believed he was so much of a scumbag he couldn’t trust him with his sister. And said guy was Chuck ‘has a 3.0 GPA but never got laid in his life’ Shurley, the same Chuck Shurley who should get on his knees and praise the lord for the miracle that was Dean blessing him with his generally more than popular attention.

Maybe Dean hadn’t said anything for too long or looked as offended ( _betrayed_ ) as he felt, but something made Chuck’s face softer, made him draw his eyebrows tight. “Dean, I, please don’t take it personal, it’s... It’s just the way she is.”

Dean’s interest quivered alive at that. Information? Yes, please.

“She has very...” Chuck looked away again, laughed, drank more beer. His head drifted around, maybe searching for words or starting to get seriously drunk or both. “... uh, high standards,” he eventually finished, not without letting out something that seemed a crossover between a sob and a laugh and a choke.

Unamused voice, slight frown. “Meanin’ _what_?” Dean knew he was handsome, _very_ handsome, and he had so much charm and knew how to treat a lady, and-

“Dean...” And Chuck said it with genuine commiseration in his wide, always watery eyes. “You’re... you’re a _mechanic_.” Forced by Dean’s baffled silence, leaning closer and on the quiet, Chuck specified, “You’re _poor_.”

So it turned out Chuck’s family earns five-digit annual salaries from interest alone, that they are all over town being involved in all kind of big shit and Dean didn’t know, because he’s, what, a degenerate of some sort for not having a decent bank balance? Chuck assured that it’s not what he meant, at least not _him_ , and Dean’s ego not only shrunk but shriveled. Didn’t help that Chuck offered to pay the next round, no, nope.

Girls who can buy every Ken doll they want don’t busy themselves with cheap Figaros.

Some jaegers and whatnot later and Dean felt like punching something, someone. Next best thing seemed to be venting. With his mouth. It’s what he does; shut up. “If you’re so super rich,” he started, slurring so hard he didn’t quite understand himself, “then why d’you look like a goddamn hobo, huh? _You_ look broke. Why you even bother workin’?”

“It makes me happy,” was what Chuck had as an answer.

Simple as that. And stupid as hell.

Chuck never shaved (or even trimmed his beard) or made effort of how he dressed. He looked like he couldn’t afford his drinks and acted like he couldn’t form full sentences. And yet, he had this secret, actually uber-interesting identity he never had bothered to share with anyone. It maddened Dean. It felt like being lied to. Were him and his friends really that judging when it came to the income question? Sure, they were all more or less on the lower edge of the wage range – Benny a colleague of Dean down at the garage, Cas some sort of ‘freelancing spiritual guide’ (Dean was pretty sure he made most of his cash through dealing), Garth and Victor underpaid cops, and Ash, well, he never specified what exactly he was doing in his ‘IT job’ but for all Dean now learned about Chuck, he could as well be just another secret billionaire – but would they have treated Chuck differently if they had known he was born with a golden spoon up his ass?

It took Dean some time to realize his own behavior was more than enough of an answer.

So, after some silence after ‘the big exposure’, he kept on texting Chuck. Meeting Chuck, hanging out. Still being low-key pissed, yeah, but the guy wasn’t to blame. He was just a sad little worm, just like Dean. Maybe money wasn’t the solution to every problem after all.

What also kind of helped was the fact that Chuck lives in one hell of an apartment. Uptown. Jacuzzi. Whole damn nine.

And that he shares it with his sister.

The day Chuck made the mistake of letting Dean crash at his place (because Dean was so drunk the only other option would have been the hospital) was the day Dean practically moved in with him. It didn’t seem to bother Chuck, which was too good to be true. And as long as it was happening, Dean wanted to enjoy it.

He started coming over right after work, every few days or so. Afternoons would spread into evenings, sometimes into nights. Dean always brought beer while Chuck always paid for pizza. Chuck owned all the gaming consoles Dean never had the spare money to invest in and new games would appear almost magically a few days after Dean would very passingly mention them. It didn’t feel like milking Chuck since Dean was investing, too. Friendship against materialistic goods – and Chuck clearly owned the things he bought, didn’t he. No... Dean definitely _wasn’t_ using Chuck.

Chuck answered every innocent question Dean threw at him – Amara’s job, her birthday, favorite meal, favorite bar (‘members only’ of course, fuck). All the newfound information had Dean’s interest spiking anew. Again, everything seemed possible. If Chuck was so deliberately sharing things with Dean, then maybe he had hope for Dean to have a glimpse of a chance. A glimpse was enough. Would _be_ enough. Dean usually needed less than that.

There was a strange expression when Dean gently rephrased his request for Chuck to introduce him. Chuck leaned back into the couch, hands in his lap and still greasy from the pizza they had finished by now. Ignoring the high quality leather of the couch and the high end sound system in the room, the two of them could have easily passed as two equally situated, equally paid people.

“Dean...” Chuck did that often; saying Dean’s name. Dean only called Chuck by his name when he pretended to be angry at him or actually _was_ angry at him; otherwise, it would just be ‘dude’. But Chuck always called him ‘Dean’. “What is it that fascinates you so much about her? I mean, I know her and I don’t see why you even bother.” Meaningless shrug. “She’s high maintenance material, not some short-time project... and you could easily have every girl out there! Just sayin’.”

Dean thought about explaining that Amara enthralled him to a point where he couldn’t even _think_ of any other girl, let alone hook up. His mouth played with phrases like ‘she’s special’ or ‘I don’t want anyone but her’, but ended up staying quiet, lips tight, obvious. He didn’t even _know_ her. How pathetic to cling to some faint fantasy he didn’t even know was possible in the very least.

Chuck didn’t make fun of him – not at all. Not even a roll of eyes, a sharp sigh. The guy is too good-minded. The good-minded always have it hardest.

They end up getting ditched. Used. Hurt.

Dean kept visiting but no matter what time he chose to show up, Amara never seemed to be home. She’d always have ‘just left’, had to catch a plane, got her nails or hair done, was shopping with a friend, had to discuss world peace, whatever fucking stupid reason.

Chuck knew something Dean didn’t, and that was certain. There must have been withheld information because this here was simply ridiculous. It hung in the air and weighed down heavier each time Amara was absent, again, and Dean was left with Chuck, again. Whenever Chuck would take a bathroom break, Dean would snoop around as much as he could, but there never was anything in plain sight and there always was too little time to dig deep enough.

Again, a blank space on Dean’s map. Where to now?

So, one month, three weeks. Felt like a lifetime, as if Dean had worked double shifts all this time (despite the opposite being the actual case – all the staying out at night led to hangovers and missed days). Exhausted but still thirsty, Chuck somewhere close and just as drunk, they ended up at Dean’s because fuck it, Amara wouldn’t be home anyway, would be banging Robert Downey Jr. or someone equally famous, rich, better-than-Dean.

It didn’t register to Dean that they were at his place until he found himself on his faithful old sofa, a skillfully rolled blunt (thanks, Cas) in his fingers, and that all seemed so familiar, didn’t it? His head was laid back against the cushions and his mouth felt awful. The blunt left his fingers and Dean listened to Chuck taking several deep, controlled lungfuls. The nerd didn’t even _cough_. Damn rich kids.

“I like your place.” Chuck is the type who would say sappy shit like that (and _mean_ it) even without being stoned.

“Thanks,” slurred Dean who felt like throwing up but also inhaling an entire pizza.

“Why haven’t we been here before?”

Dean coughed a dry laugh and sucked greedily on what he retrieved. The room was spinning in a comfortable speed and Dean smiled for that with his eyes closed. “’Cause it’s a raaaaat hole.” The sound of Chuck moving around, maybe getting up, only made Dean giggle more. He took another few hits, just because.

“Why would you say that?” Chuck sounded far away. “It’s cozy. I like it. It has a certain... charm.”

The last comment made Dean laugh so hard he threw up. That must have startled Chuck but Dean faintly remembers falling asleep (or unconscious) to the sound of both their breathless laughter.

Whatever it was – maybe Cas had hid some molly in Dean’s coffee, maybe Chuck had a weird ‘disgusting rundown flats’ fetish or maybe, just maybe, things were finally starting to work according to Dean’s plans – that made Chuck smile and speak that next morning, Dean had no idea.

“I told her about you recently,” and Dean remembers clearly how ethereal Chuck looked with the hangover-shadows underneath his eyes almost down to his knees, with the steaming cup of boiling hot and murderously strong coffee in his hands, and that stupid, stupid child-like smile of his, “and, well, I, of course I played down the, the minor details, but... she didn’t seem... completely disgusted? If that means anything to you.”

It was the beginning of something new, something beautiful. Dean just _knew_ it. Finally. It would all pay off. All the wasted time, all the waiting and hoping – his foot was so far in that door that someone would have had to chop it off to get it out. Of course Chuck would have talked about him with Amara. She must know that there’s a wonderful, handsome, caring guy who spent time with her pitiable brother. That he was single and so fucking ready to mingle. It only seemed a small bite in the ass that Chuck hadn’t discussed these steps with Dean prior to executing them. Dean could forgive him for that; at least since everything was working out. Yes.

Things went fast. Almost too fast for Dean to realize, to get ready.

A regular Wednesday – Chuck’s place and beer and chicken wings, the good jeans because maybe they would be going out later that night, the tight shirt because Dean felt awesome again after weeks of desperation. The sheer idea of Chuck presenting him with new facts about his sister were enough to catapult Dean’s spirits into once so familiar heights. He could get it all back. His reputation – his pride – his mojo – all of it. He felt _good_.

The TV was running, wings ordered, first two beers empty on the way too fancy coffee table (it’s just a place to put your feet and/or beer, for fuck’s sake, why would that need to be costing hundreds of dollars?), and Dean felt super, sup _erb_ , and Chuck was easy as always, chatting away, and Dean almost was inclined to actually listen. Chuck’s phone going off somewhere in the entirely other corner of the apartment stopped him, though. Chuck bolted off and Dean was alone, not drunk enough, too giddy to sit still. He tapped away on his phone just to busy himself, without really needing to check any messages. And then, something changed.

It was a true sensation, almost a thrill, a warm weight settling over everything in the room. Dean didn’t dare moving until his instincts told him that he was being watched. So Dean turned around.

There, in the open space connecting kitchen, living room and corridor, stood Amara – and watched him.

Something in Dean wanted to scream from the surprise, but something different wouldn’t let him make a single sound, let alone move a muscle. He knew his eyes were wide, that he was staring and that it was rude, but he couldn’t help himself.

She was even more beautiful than he remembered her. Her black high heels still casually held in one of her elegant hands, the light from the TV in the far front and from Chuck’s room in the far back painted a surreal picture against her slender silhouette. Loose hair, heavy make-up, one delicate necklace and bracelet – tight, black, knee-length and sleeveless dress. Bare legs. Bare feet.

She was a goddess.

Dean still couldn’t speak. She looked straight at him, into his eyes, again, and Dean had so much time here and now but couldn’t say a damn word. The fact that she was here, that she didn’t bolt off right away at the sight of him – it seemed like a dream. You wake up if you move too hard. Just let it happen.

She stared at him for another while before slowly coming into motion. There barely was a noise of her bare feet on the tiles against Chuck’s troubled phone call across the corridor, against the noises from the TV. She must have slipped in with her shoes off, Dean concluded. If she had returned from some party, some event? The two of them held eye contact this whole time, maybe equally fascinated, but faced with the woman he had been thinking about non-stop, Dean felt more like prey than anything else.

Eventually, she vanished around a corner, just like that, and Chuck returning to Dean’s side made him jolt, hard, and curse, hard.

Chuck laughed about as long as it took for Dean to hiss, “Dude, she’s _here_!” That, for some reason, shut him right up. Actually (but maybe Dean was only projecting his own terror upon the guy), he was even turning pale. “Dude!” Dean repeated, more insistent this time, as if it would help with anything, would solve anything.

“I, I didn’t- I had no idea she...”

Dean’s insides flashed ice-cold. “Ohmygod, I don’t even, I’m not even wearing my best- ohshitfuckgoddammitfuck-“

Something in the corner of their eyes caught their attention, and to the general surprise it was an arm belonging to neither of them, reaching out towards them – grabbing a beer, drawing back.

“Move.”

They parted like the goddamn Red Sea.

She sank between them, enough polite space for her not to be touching Dean. He kept staring, gaping. Her scent was overwhelming, just like the finer details of her face Dean could make out in the low light now. She was facing forward, granting the TV her silent attention; ignoring the other two people in the room with her. The beer had already been opened before she had grabbed it and she held it to her mouth to wrap her lips around it. This entire thing only made her a thousand times hotter. She probably sipped nothing but champagne, at least looked and dressed like it, but a girl with a taste for beer? God, Dean was so in over his head he was close to tears.

Dean blinked, felt sweat building everywhere on his body, his cock giving a faint throb because Amara’s pursed lips were _wrapped around the damn bottle neck_ , and he couldn’t shake the wondering about whether this was her lips’ natural color or if it was lipstick, if her cheekbones _were_ that impressive or if it was make-up, if she was the type who’d keep make-up and lingerie on while fucking, god, fuck, Dean was so _done_.

He suddenly remembered Chuck. That Chuck was here, too, and that Amara was his _sister_ and that Dean was his _buddy_ , and that Chuck _was supposed to fucking help him out here_.

Okay. So Dean would have to speak up.

Uhm. Okay.

Sounded easier than it would be done with his heart somewhere up his teeth, his hands shaky and sweaty, his throat so dry he had to clear it twice before getting out a single syllable. “Uh, Chuck, you, uh, you know, _mind_...?” A vague gesture between Amara and him, the try for a sly smirk, a cocked eyebrow; his usual repertoire. It all felt ridiculous now.

Chuck was looking at him, his eyes as wide as usually – his lips drawn tight. No movement. No word.

Just when Dean started noticing how close the siblings were sitting and in turn zeroed in on Amara’s free hand resting on top of Chuck’s thigh, Amara put down her beer to say, “Don’t bother. He won’t speak unless I tell him to. Besides, I already know who you are.”

If the smirk had been there in the first place, it had vanished at this point. Dean blinked, eyes darting between brother and sister (not the hand or the closeness, nonono), trying to make a sense out of it, furrowing his brows, hard. He opened his mouth just to have a hand clamped over it.

Instinct made him pull back, but the hand followed, pressing down with intention. “I made it a rule because I hate dumb babbling, Dean-” Oh god, his name from her heavenly mouth...! “-and I have a feeling you are one _very_ dumb babbling person. So I’ll save us all some time and tell you to _shut the hell up._ ”

Her hand withdrew. Dean squinted his eyes, took a small breath and started with, “But-“

“A-sh-sh-sh.” The hand was right back. Shit, the girl was quick. He kept up their eye contact but never ever was his gaze as intense as hers – completely unbending. “Don’t test my patience.” Felt like a warning. Kinda made Dean want to lick her palm.

Her touch had Dean elated. He wasn’t aware of how quickly he had started to relax under her eyes, her hand, the firm pressure of both keeping him in place. Eventually, he let out a remotely deep exhale through his nose and that made Amara take off some force from her hand.

For some reason, Dean really really expected a ‘good boy’ from her then.

“My brother told me a lot about you.” Her voice reverberated in Dean’s head, his entire body. She spoke so quietly, so calmly, that the TV almost was enough to overpower her. Was it just him or did her expression soften just now? “He showed me photos, too.” Very, very softly, her hand drifted from Dean’s mouth, sideway, turning. She ran her knuckles along Dean’s jaw, his cheek. Dean felt like melting under the touch. “He didn’t lie... you _are_ pretty.”

Dean’s eyes slipped shut for a moment. Chuck had told her good things. He had praised him in front of Amara, marketed him like he needed to be, how it was right to be done. It all came together now, to this – victory.

Dean had almost felt like smiling again but opened his eyes just in time to see Amara slowly leaning forward, towards his face, and instead he decided to abandon every thought to savor what was about to happen.

Don’t stir. You’ll wake up.

As she kissed him, her hand was still resting on his cheek, cupping it softly, bleeding warmth into Dean. She must have been feeling his sweat, must have been tasting the beer and earlier dinner on him, must have smelled his cheap cologne and aftershave. And yet, she kissed him.

Dean’s eyes drifted close once more. Everything else seemed impossible, a waste. He wanted to feel nothing but her – her touch, her lips, her skin. She drew back a little just to have him leaning in for a chase, to come back to him. Slow and tender, it was just right, matched her, _them_ , Dean and her, because they were meant to be, weren’t they? With a kiss like this, you can’t fool anyone.

They parted for good (hopefully only for now), him dizzy and starry-eyed and she looked rather unimpressed but Dean could tell there had been a change – an even softer tone to her face, heavier lidded eyes. God, yes. She wanted him, too.

She has beautiful fingers. She fanned them over Dean’s cheek and temple, ran her eyes over his features. Even though people ogled him all the time, Dean rarely ever had felt as undressed by someone’s eyes as in this very moment with Amara.

Her fingers reached into his hair, around the back of his head, and as she started pushing him forward and definitely not into her face, more in front of her, Dean watched her say, “Your turn.”

Where he had been oddly calm up to here, Dean was full-on bewildered once more. Her words didn’t make sense, absolutely didn’t, until Chuck kind of emerged from the shadows she was casting, started coming towards Dean with his face and _what the fuck was going on here?!_

“Woah, nonono, time-out, time-out!” He tried to get out of her grip but she only fisted his hair harder, so he searched for her eyes for an explanation, an excuse, anything. There was nothing for him – Amara stared blankly, tenser than before. Maybe a little pissed. Nervous panic started making its way through Dean’s system. A choked laugh, more sweat. “Fuck, I’m- I’m not into dudes, I, Ch-Chuck is just a, just a friend, I-“

“Do I look like I care?” She certainly didn’t. Dean weakly shook his head. “And moreover – did I stutter when I said you stay quiet? If you can’t stick to the rules, I’ll have to ask you to leave.” The urge to object was strong, but oh god... “Do you want to leave, Dean? Answer.”

Dean’s throat bobbed with the tightness he felt. “No,” he croaked.

“Then do. What. I. Say.”

Shit. Shit shit shit.

Was this what being in love felt like?

So Dean is kissing Chuck now, tongue and all, because the hope that Amara will make it up to him is present and sitting right in his lap, so close, and Chuck at least is quiet so it’s easy to pretend as long as Dean ignores the beard. Just a kiss. Dean can do a damn kiss.

Things get better when they start taking turns, Amara always the one to decide with her hand still in Dean’s hair, and that shouldn’t be hot, shouldn’t even be possible but maybe Dean’s last haircut was too long ago because buying beer was more important (he honestly can’t remember). Dean goes with it, savors her taste in his mouth despite Chuck licking it out of him soon enough. He is hard from making out alone. God, he wants to undress her so bad. Or maybe just feel her up over her clothes, doesn’t matter, just something, anything. His hands won’t make a move though – he isn’t crazy.

Dean can be obedient when he has to.

Amara pushes one hand up against Dean’s chest. “Stand up. Undress.”

Dean is on his legs instantly but wavers when he’s there, right in front of both siblings, his hands already on the hem of his shirt but damn, this is so weird. So so fucked up. He checks between Chuck and Amara, sees her hand still on his thigh, no, higher, almost bumping against Chuck’s crotch and is that- oh fuck no. And both have their eyes on him, waiting. Expecting.

The shirt is up and over his head while he mutters to himself how he can’t believe this, and he feels a hot rush into his face when he flings the shirt away because fuck, he isn’t supposed to talk. Amara doesn’t correct him though and that’s... actually a tie between relief and disappointment. Dean knows both of them can see the bulge in his jeans, knows they both have their eyes plastered where he struggles with the belt first and buttons later.

“Everything,” Amara specifies.

Dean cringes but shoves his thumbs from over to under the elastic of his boxers to push down everything at once. He bends down to get it all to his ankles and pretty much inelegantly forces his feet out, too. He’s not drunk enough and too pent up from the last weeks, had showered but not trimmed, doesn’t feel a hundred percent confident like he should, like he can, and he uselessly rubs his hand over his nose in an attempt to hide (if only a little bit).

Amara lets him cook for another torturous moment before signing him over to her with a curl of her forefinger. He straddles her, just going for it, she can still correct him after all, but she lets him and even lets him kiss her, lets him curl over her, his elbows breached on the back of the sofa. Both of her hands slide up his thighs, easy and light, up his flanks and that makes Dean shudder. Her nails are painted black, long and perfect, and only the slightest pressure turns a tickle into a faint scratch. Dean groans for that. He groans again when she finds his nipples and tweaks them not too gently. He arches his back. God. He’s gonna ruin her dress if this goes on.

Amara keeps teasing and when Dean risks a peek she is kissing with her eyes open, watches him, and he squeezes his eyes shut again immediately. His insides are curling, burning, and he doesn’t need much more, just, just...

Dean’s hands go from sofa to Amara’s shoulders to push the straps of her dress down but that’s when a third hand pinches the back of his neck, hard, hard enough to make him hiss. Even though he pulled his hands off immediately, Amara whispers against his mouth, “You won’t touch anyone, not even yourself, unless you’re told to.”

Dean groans loudly.

“That’s right.” She sounds like she’s smiling. “Not used to that, aren’t you? So used to always getting what you want...! A spoiled puppy, that’s what you are.” Amara’s lips run down Dean’s cheek, chin, start kissing his throat. He bares it happily, desperately. Yeah. He can feel her smiling. “Good puppies get treats though. If you’re good and listen to what I say, we’ll have lots of fun. Does that sound good to you, Dean?”

“God, yes.” She’s still kneading his nipples.

“When I ask you a question, you nod or shake your head.”

With his bottom lip caught between his teeth, Dean nods eagerly.

“Good,” Amara hums, “because I think I have far better use than talking for that mouth of yours.”

Dean’s balls throb for that. God. Yes. Please.

Amara’s hands span wide over his pecs, his hard and by now aching nipples in the center of her palms. The warmth is heavenly. He is too out of it to even think to keep kissing her.

“Have you ever had your ass played with, Dean?”

He tenses visibly.

“And I don’t mean a fingertip. Had it licked? Fucked?”

Dean’s stomach cramps as his erection droops. He really really doesn’t like where this is going. He keeps his eyes closed, brows tense, and shakes his head.

“Shhh, hey.” Her hands travel to his sides, run up and down. Kisses come back, press themselves along his collar bones. He can feel his chest heaving against her chin. “Don’t be like that. You’ll like it. He’s good. I taught him.”

A hand lays itself on his lower back, wide and warm, and all of this is all kinds of wrong. Dean’s head is swimming, his ears ringing, and he feels like crying and thrashing but he’s also so so turned on, so unwilling to give this here up, to give up Amara – to displease her.

Dean knows it’s Chuck moving behind him even though he hadn’t heard him get up in the first place. That hand slides lower. Amara cups Dean’s face with both hands now, pulls him down to her, pecks a kiss to the side of his mouth which is already sliding open. “Here, keep kissing me. Relax.”

Dean does that. Kisses and kisses until he doesn’t see Chuck’s face in front of him anymore, until it’s just some anonymous hand feeling him up. The sensation of fingers sliding along the cleft of his ass is intense, weird, a little sickening, but it’s also slow and reminds Dean of Amara’s touches and that makes it easier. When it becomes a thumb massaging down on his asshole it’s too strange though. Dean tries to rearrange his position to make it less awkward but he has not much space to work with, feels on display, needs Amara to get undressed already, wants to touch her. The kisses have him riled up and fully erect again. He tries hard not to let his bare cock touch her dress (he couldn’t afford the dry cleaners, probably).

It only registers to Dean that the sound that appears means Chuck is getting to his knees when there’s already a tongue lapping at him, and that absolutely makes his eyes pop open, his body humping forward, away, but Chuck pulls him back by his hips and Dean has to take it. Amara keeps kissing him through it and her fingers return to work his nipples. Dean has no control over his senses and is overwhelmed by waves after waves of goosebumps caused by the alien friction of a rough beard against the tender insides of his thighs, the slick, hot movements of that tongue slowly kissing itself into his ass. Fuck. Shit.

He’s gonna get his ass fucked tonight. So very not what this was supposed to be like.

Amara praises, “Very good,” almost sounds surprised, and Dean lets out a ragged breath with her hand on his cheek, her teeth on his earlobe. He hears fabric rustling somewhere close, between them. His eyes open just in time to watch her rucking up her dress. “Good enough for a treat. Get down there.”

His knees have barely hit the floor and she is still not done shoving her dress up but his face is already buried between her thighs, in her already soaking pussy. She was commando under her designer dress all along and she’s waxed smooth except for a broad stripe of hair up her pubis and it’s no shame at all to be moaning with his lips sealed around this paradise.

Her thighs part wider while she lets out a pleased sigh and she scoots down the sofa some more to give Dean more access which he promptly claims, lets her rest her feet on his shoulders and puts his hands around her thighs to anchor himself so he can dive in even better.

This. This is what he’s good at, _truly_ good at. He doesn’t need to talk to swoon her anymore – he has his chance right here.

The sanctuary of the moment quickly is disturbed by that damn mouth up his ass once more, fiercer this time, harsher, and a finger pushing in next to a tongue has Dean gasping involuntarily. Amara grabs his hair again, one hand only (only _needs_ one hand to keep him in line, doesn’t she?), and pulls Dean in harder, urges him to keep going. He does his best, suckles on her clit, runs his lips along the folds of her pussy, flicks and rolls his tongue but the burn in his ass is ever-present, won’t let him be unconscious of what is going on anymore. He can hear Chuck’s breathing, hears him clicking open what must be lube, and yeah, slick and cold and the finger is alone now, deep, deeper, and then it _curls_ and Dean’s body surges forward with a shudder, into Amara’s lap. He whimpers because it feels disgusting and absolutely not right, but Amara shoves his head back between her thighs and keeps him there with force and both hands until he’s pliant again, licking her, drowning in her.

“Maybe I’ll let you take off my dress later,” Amara muses slightly breathless somewhere far away, so far away Dean feels like crying like a child, but the thought of her bare tits is enough to keep him in place instead of bolting away and running for the door when Chuck starts to push his cock up Dean’s ass.

Dean gasps and splutters and chokes on his spit and her juices but she keeps him right there, right where she’s wettest and hottest and needs him most, and he would give her anything, everything, he truly would. He growls (it fuckin’ _hurts_ ) and she smacks his head, grinds her pussy up against his mouth and mutters what must be an encouraging, “Come on.”

Dean lets Chuck press inside until their bodies rest against each other, until he’s shaking from the stretch, the burn, until the scent of lube and latex reaches his nose despite being smashed up against Amara’s pussy. He can hear Chuck exhaling with a stutter, always stuttering, that damn nerd, but those hands are steady and manipulate Dean’s hips into tilting low, sticking his ass out, presenting. Nervousness has Dean tense, so tense, softly shaking from the exertion of staying put, taking it, and he keeps working his mouth because it’s the only damn thing he is allowed to be doing.

The first few strokes are painful and slow. Feels like being pulled inside-out and smells like it, too. Dean falters in his breathing, his efforts to please Amara, so she keeps smacking the top of his head, humps his face. He groans and hates, wants, his eyebrows knitted tight on his forehead, sweat beading and rolling down on his temples and he is getting his ass fucked by motherfucking Chuck ‘isn’t it way past your bedtime, young man?’ Shurley.

It should worry him. The lows he is ready to sink to to get what he wants; to get _who_ he wants. That he gives so much power over himself to other people so easily. That all it takes is a big bunch of disinterest to have him begging, out of his mind, on his knees.

Maybe Dad was right with his weekly (daily?) talk about Dean having no dignity.

For someone who doesn’t look like he could handle a simple kiss to the cheek, Chuck seems to know exactly how to (a) fuck and (b) fuck very well; if Dean would call it “well”, that is. It’s hard and fast sooner than Dean could prepare for it and gets him by surprise each time Chuck’s cock ruts right across his prostate, has him jolt and tense, slip, makes it hard to concentrate on the pussy he is supposed to be eating. His tongue is out anyway if he likes it or not, mushed up against Amara and maybe worryingly numb.

Dean hears himself huffing weird sounds, noises; something between grunts and whines and it’s humiliating to say the least – but Amara seems to purely love it. She’s breathing harder by the minute now, getting wetter, too, and fuck, this turns her on, doesn’t it? Two guys getting it on right in front of her. Or maybe two guys acting out her very words? Or one of them being her brother? Or one of them being Dean?

“Touch yourself,” Dean hears, and his first instinct is to laugh because how the fuck could he be hard while being fucked by a guy? But when his hand reaches down and out, shit, then he’s dripping all over the floor tiles, moaning at how good his own hand feels on his too-long neglected cock. So good, actually, that he thinks he could come. Could come _real soon_. Fuck.

It feels so fucking good, so low and just right that even whatever Chuck is doing to him becomes better, real good, like his dick being teased from the other end, _from inside_ , and Dean whirls his palm over his wet cockhead just like he whirls his tongue over Amara’s clit. Chuck’s rushing now, panting hard, hints of his voice Dean has heard so many times in these past weeks sweetly peeking through, sounding almost painful.

“Yes,” Amara rumbles, choked-up and god she’s burning up under Dean’s mouth, “yes, do it, go ahead, go ahead...!”

Dean knows she’s coming because she holds her breath, because she’s so damn wet it’s running down his chin now, her thigh shaking apart in his hand, and when she snaps for a breath there’s this high-pitched whine from her and that’s what shoves Dean over the edge himself; hard.

With her still crushing his face into her and Chuck still pounding him forward, Dean groans from somewhere deep in his chest, his belly, as he shoots his load onto the tiles and his own hand.

“Fuck, Dean!” And that’s Chuck, Chuck now really losing it, ramming into Dean so hard it makes everyone’s teeth rattle (but especially Dean’s), makes Dean’s cock keep spitting even though there shouldn’t be anything left, and maybe Amara comes a second time but Dean can’t think, can’t pay attention to anything but the crushing heat in his insides, twisting and pushing and making him lose it.

It dies down slowly, eventually. Dean muses that Chuck must have come inside the condom at some point but doesn’t go soft just yet, rides it out, and Dean likes to do that too when he has the chance. Amara lifts his head by his hair to sign him that it’s enough, it’s done, and Dean takes a first full breath since forever. The cold air hitting his soaked face brings back some sense, makes him almost want to blink his eyes open, but maybe not just yet. Just another moment of headless bliss.

He makes a pained sound when Chuck slips out for good. Fuck, how do people take it up the ass regularly? Does it even go back to normal? Dean wants to curl into a ball on the floor but slips right back onto all fours when the tiles are way too cold to let him go through with his plan in any form of comfort. Catching his breath, head hanging low, Dean feels himself shaking from exhaustion. Despite everything, the afterburn of his orgasm is perfect. Delicious.

“Okay everyone,” Amara huffs, swings her legs over Dean to get to her feet. As she makes her way to presumably the bathroom, Dean can hear the zipper of her dress being undone. “Five minute breather. Brother, you spoke without permission. Dean, you ever fucked anyone up the ass?”

The shower starts up and Dean looks back over his shoulder, finds a flushed and sweaty Chuck who is sitting on his ass on the goddamn ice-cold tiles, grinning like a fool, and Dean gives him the most irritated look.

“Sorry,” Chuck whispers, quiet enough for the shower and distance to keep it a secret from his sister. Something – maybe the fact that that grin is showing no signs of vanishing anytime soon – tells Dean that the guy doesn’t mean it.


End file.
